An N-heterocyclic carbene-catalyzed atroposelective [3 + 3] annulation of enals with 2-aminomaleate derivatives is described. A series of substituted dihydropyridones bearing both C-N axis and point chirality were synthesized with good diastereo- and enantioselectivity under mild conditions. This efficient strategy successfully superpositions an extra point chiral element with an axial backbone, and the generated structurally interesting atropisomers may have potential application in drug discovery.